Efficient synthesis of (2R,3R)- and (2S,3S)-2,3-diaminobutane-1,4-diol and their dibenzyl ethers

Tetrahedron Asymmetry

Volumn 8, Issue 8, 1997, Pages 1243-1251

  Scheurer, Andreas ^a   Mosset, Paul ^a   Saalfrank, Rolf W ^b  

^a CNRS   (France)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANEDIOL DERIVATIVE; DIAMINE;

ARTICLE; CHIRALITY; DRUG PURIFICATION; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030934355     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00086-4     Document Type: Article

References (34)

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9. (2S,3S)-1,4-Diaminobutane-2,3-diol was prepared from L-tartaric acid (D. E. Kiely, J. L. Navia, L. A. Miller, T. H. Lin, J. Carbohydr. Chem. 1986, 5, 183; (1R,3R)-2,4-diaminobutane-1,3-diol and (1S,3R)-2,4-diamino-butane-1,3-diol were prepared from D-glucose and L-arabinose respectively (R. Jiricek, J. Lehmann, B. Rob, M. Scheuring, Carbohydr. Res. 1993, 250, 31).
10. (2S,3S)-1,4-Diaminobutane-2,3-diol was prepared from L-tartaric acid (D. E. Kiely, J. L. Navia, L. A. Miller, T. H. Lin, J. Carbohydr. Chem. 1986, 5, 183; (1R,3R)-2,4-diaminobutane-1,3-diol and (1S,3R)-2,4-diamino-butane-1,3-diol were prepared from D-glucose and L-arabinose respectively (R. Jiricek, J. Lehmann, B. Rob, M. Scheuring, Carbohydr. Res. 1993, 250, 31).
11. S. Hanessian, T. Theophanides, Can. CA 1282058 (Chem. Abs. 116, P 119763e); S. Hanessian, J.-Y. Gauthier, K. Okamoto, A. L. Beauchamp, T. Theophanides, Can. J. Chem. 1993, 71, 880.
12. S. Hanessian, T. Theophanides, Can. CA 1282058 (Chem. Abs. 116, P 119763e); S. Hanessian, J.-Y. Gauthier, K. Okamoto, A. L. Beauchamp, T. Theophanides, Can. J. Chem. 1993, 71, 880.
13. (+)-Diethyl tartrate was converted to 2,3-O-isopropylidene-D-threitol according to A. Holy, Collect. Czech. Chem. Commun. 1982, 47, 173 (acetalization by triethyl orthoformate and acetone followed by reduction of ethyl ester groups by sodium borohydride in absolute ethanol). Further transformation into diol 2 was performed according to E. A. Mash, K. A. Nelson, S. Van Deusen, S. B. Hemperly, Org. Synth., Coll. Vol. VIII, 1993, 155. Diol 2 is also commercialy available from Aldrich or Fluka.
14. (+)-Diethyl tartrate was converted to 2,3-O-isopropylidene-D-threitol according to A. Holy, Collect. Czech. Chem. Commun. 1982, 47, 173 (acetalization by triethyl orthoformate and acetone followed by reduction of ethyl ester groups by sodium borohydride in absolute ethanol). Further transformation into diol 2 was performed according to E. A. Mash, K. A. Nelson, S. Van Deusen, S. B. Hemperly, Org. Synth., Coll. Vol. VIII, 1993, 155. Diol 2 is also commercialy available from Aldrich or Fluka.
15. T. Oishi, M. Hirama, Tetrahedron Lett. 1992, 33, 639.
16. Compounds 2, 3, and 4 were also prepared in racemic form butadiene diepoxide [M. T. DuPriest, B. M. York Jr., US Patent 4,659,733 (Chem. Abs. 107, 77816f)].
17. 12 proved to be more convenient and efficient.
18. M. S. Congreve, E. C. Davidson, M. A. M. Fuhry, A. B. Holmes, A. N. Payne, R. A. Robinson, S. E. Ward, Synlett 1993, 663.
19. 13C NMR and HRMS indicated that it could be the N,N′-dimethyl derivative of 6. Its formation could be explained by the following side reactions: dehydrogenation of methanol by the catalyst to give formaldehyde, nucleophilic addition of formaldehyde to the primary amino group of 6, dehydration of the resulting aminoalcohol to yield a putative intermediate methylene imine which would be hydrogenated to give a N-methylated amine. Adams' catalyst afforded 6 with only a neglectible amount (ca. 5%) of this by-product.
20. Catalytic hydrogenation of diazide 8 only afforded a complex mixture instead of the desired diamine.
21. P. H. J. Carlsen, T. Katsuki, V. S. Martin, K. B. Sharpless, J. Org. Chem. 1981, 46, 3936; P. F. Schuda, M. B. Cichowicz, M. R. Heimann, Tetrahedron Lett. 1983, 24, 3829; M. T. Nuñez, V. S. Martin, J. Org. Chem. 1990, 55, 1928.
22. P. H. J. Carlsen, T. Katsuki, V. S. Martin, K. B. Sharpless, J. Org. Chem. 1981, 46, 3936; P. F. Schuda, M. B. Cichowicz, M. R. Heimann, Tetrahedron Lett. 1983, 24, 3829; M. T. Nuñez, V. S. Martin, J. Org. Chem. 1990, 55, 1928.
23. P. H. J. Carlsen, T. Katsuki, V. S. Martin, K. B. Sharpless, J. Org. Chem. 1981, 46, 3936; P. F. Schuda, M. B. Cichowicz, M. R. Heimann, Tetrahedron Lett. 1983, 24, 3829; M. T. Nuñez, V. S. Martin, J. Org. Chem. 1990, 55, 1928.
24. Purchased from Fluka.
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27. 25 On the other hand, a lanthanide shift experiment was inefficient since no splitting of signals was observed when adding Eu(tfc)3 to a mixture of 5 and its (2S,3S)-enantiomer.
28. 1H NMR spectra of these compounds, a symmetrical six spins ABCC′A′B′ system was observed. Simulation afforded the following NMR parameters Table 1).
29. In spite of the high N/C ratio of 5, suggesting a potential explosive hazard, no problem was encountered. However caution is recommended in handling 5.
30. Specific optical rotation of bis-aminoalcohol 6 could not be measured in water since the aqueous solution of 6 was turbid even after filtration through celite.
31. withNH=6.0 Hz.
32. For example, see N. Ikemoto, S. L. Schreiber, J. Am. Chem. Soc. 1992, 114, 2524.
33. T. Akiyama, H. Hirofuji, S. Ozaki, Tetrahedron Lett. 1991, 32, 1321.
34. H. Abdallah, P. Messet, unpublished results.